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JOURNAL OF ORGANIC CHEMISTRY
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02153
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A transition-metal-free method for the direct synthesis of heteroaryl sulfoxides has been described. By using fi-sulfinyl esters as the source of the sulfenate ion and a Bronsted base catalyst, the desired heteroaryl sulfoxides were obtained in yields of 30 to 94%.
Heteroaryl sulfoxides are an integral part of several bioactive molecules and pharmaceuticals. We have described a transition-metal-free route for the direct sulfinylation of 2-halobenzothiazoles and 2-halobenzimidazoles using fi-sulfinyl esters as the source of the sulfenate ion in the presence of a Bronsted base such as LiOtBu, and the corresponding heteroaryl sulfoxides were isolated in yields of 30 to 94%. Moreover, we hypothesized a plausible concerted nucleophilic aromatic substitution (cSNAr) pathway for the direct incorporation of sulfinyl functionality into the 2-haloheteroarenes.
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